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The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Khe Hy, Ben Hunt, Wade Foster, Dan Vassallo, Kris Abdelmessih, Steph ...
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How I Write is about helping you find what works best for your own writing. You can read what an author writes anywhere, but only on this show will you hear how they write. This show isn’t just about methods and styles, though. It’s also about what it means to be a writer today. How can you earn a living? What about building an audience? Should you use GPT? How I Write is your compass for navigating these changes. It’s a show by writers, for writers, built for the age of the Internet. New ep ...
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riseyear

Taylor Marks

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A curious twenty-something navigating what it means to grow up, how people choose the careers they do, and along the way answering her own questions about failures, dreams, and identity. Support this podcast: https://podcasters.spotify.com/pod/show/riseyear/support
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Conversations

Eclectic Spacewalk

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Eclectic Spacewalk presents "Conversations" : a podcast about the uniqueness of the human condition & value systems construction - through conversation. The goal of this podcast is to have conversations with unique humans. Eclectic Spacewalk means: "a broad & diverse range of Earth philosophies viewed from outer space." You can subscribe to our newsletter here: https://eclecticspacewalk.substack.com/ Everyone has a subjective awe-inspiring viewpoint on this reality! We want to talk with anyo ...
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The Expandable Mind is hosted by Vahin Naka - an A-level student, creator and innovator. In the podcast he talks to entrepreneurs, authors, academics, medical professionals and authors on their relationship with mental health concepts and concepts in general life, like burn out, self-doubt, entrepreneurship and criticism. In the podcast he talks with the guests about these concepts through the journey’s of guests and how they have tackled and overcome them and how you could possibly apply so ...
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Scott is a cocktail of crass humor, brutal honesty, and millionaire advice. He spent ten years wanting to write a book, and when he finally did, everything he learned could be summed up into two words: Be fearless. So buckle up — because today, you’re going to learn how to write fearlessly. In this episode, we break down the nitty-gritty mechanics …
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Two words: Storytelling. Masterclass. Yeah, yeah, we know — “become a better storyteller” is probably the most basic writing advice out there. But this episode is far from basic. It’s all about the storytelling advice you actually need that you didn’t get in school. Once upon a time, Nat wrote online SEO blogs: simple, generic, and kind of boring. …
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Sign Up for "Writing Examples" and Learn From The Best Writing of All Time: https://www.writingexamples.com Ryan Holiday is one of the world’s most prolific writers. He’s published sixteen books, written a daily email newsletter every day for the past eight years, has 1.7 million YouTube subscribers, and runs his own creative agency. (Reciting that…
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Jerry Seinfeld taught me more about writing than all my English teachers combined. People forget that comedians aren’t just jokesters — they’re writers. And with 10 Emmy Awards, 3 Golden Globes, and a TV show that’s generated over three billion in revenue, it’s safe to say that Jerry Seinfeld is a dang good one. In this episode, I share the top ten…
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Cate seemed to be fully entrenched on the default path — she had graduated from Yale and became the Supreme Court advocate on her way to becoming a partner in her law firm. But she didn't want to live the lives of the people around her. She pivoted hard, you could almost hear car brakes squeaking as she made the turn, and over a year she became the…
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You may know Ted as a music historian, and the go-to expert on jazz. Or, you may know him as The Honest Broker on Substack. Either way, he’s the most erudite guest this show has ever seen. Ted gives a masterclass on the state of our culture at large. What’s up with our obsession with minimalism? Why do we value speed over beauty? Do we even realize…
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Get ready to swap everything you know about business-writing for an unconventional approach that actually works. Basecamp CEO Jason Fried is one of the world’s most successful software entrepreneurs. And he’s unique for the way he challenges the tenets of Silicon Valley startups. He’s bold like Bezos, but relaxed like Buffett. He cares less about “…
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This is from Sky King's podcast: https://skmp.supercast.com/ Guest info: Nat: https://www.nateliason.com/ Nat also has an amazing book coming out which I highly recommend, "Crypto Confidential": https://amzn.to/44BJ74I 📕Buy Paul’s Book (50k+ Sold): The Pathless Path 😁 Join Hundreds On Unconventional Paths: Pathless Path Community 📲Connect + Follow …
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From frustrated middle school teacher to Chief Evangelist at Synthesis School. From 46 email subscribers to 165,000. From hating writing to publishing her first book with a major publishing house: The Learning Game. What made all of this possible for Ana Fabrega? She unlearned how to write. In this episode, Ana shares the seven writing principles y…
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This is business writing like you’ve never seen it before. Sam Corcos is the founder of a $300 million company called Levels. He’s built a culture of intellectual rigor by hiring excellent writers and giving them time to think on paper. But don’t get it twisted — a successful “writing-first work culture” is far more than grammatically correct Slack…
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“I’m not writing for you.” This was Paul’s response to a scathing critique that came early in his writing career. Since then, Paul’s book, The Pathless Path, has sold over 50,000 copies and has spurred thousands of writers to forge their own path forward — scathing critiques and all. Writing isn’t about building the biggest readership possible. It’…
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Justin is a former startup executive who helped build two startups past valuations of $1B, teams of 150+ people, and raise over $300M in venture capital. Now he’s building his one-person knowledge business toward $5M in annual profit. 🎥🍿 YOUTUBE: WATCH HERE Links: Personal website LinkedIn X (Twitter): @thejustinwelsh The Creator MBA The Saturday S…
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There is an intrinsic interestingness inside of you. But, you’re probably suppressing it. Welcome to 96-minutes of learning how to use your interestingness to stand out online. Speaking of standing out, Steph Smith: Hosts a16z, a top five technology podcast Taught herself to code and launched multiple websites that hit #1 on Product Hunt Sold over …
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Writing is thinking, which means it’s like lighter fluid for business growth. Brie has played major roles at writing-rich companies like Stripe, and her expertise on writing-first culture is now used by giants like Amazon and Basecamp. As she says: “Reality has a surprising amount of detail.” Writing illuminates all the interesting details worth pu…
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Henry is a writer, speaker and brand consultant. He joins the podcast to discuss his upcoming book — Second Act — in which he analysises the phenomenon of late bloomers and what we can learn from them. 🎥🍿 YOUTUBE: WATCH HERE Links: Personal website Substack: The Common Reader X (Twitter): @HenryEOliver Second Act ⌛TIMESTAMPS (00:00) - Intro (01:11)…
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Paul Graham is one of the most successful writers and entrepreneurs in Silicon Valley. Sure, he sold a company to Yahoo and co-founded Y Combinator, which has created hundreds of billions of dollars in value. But more than that, Paul is a renowned essayist and his thoughts on what makes good writing are worth paying attention to. So, how has writin…
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Neil writes about all the icky, taboo things you’re not supposed to say out loud. As the author of ten New York Times Bestselling books, he’s built his career on getting celebrities like Rick Rubin, Kevin Hart, and Jenna Jameson to open up in a way that most writers are too afraid to do. But don’t get it twisted — “being vulnerable” doesn’t mean “w…
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Matt Bateman has a PhD in philosophy. He has abandoned the academic career, to pursue education in the Montessori system. A dad of three, he is passionate about educating children. Having worked a lot with training the teachers in the Montessori approach, he has now taken a step back to focus on writing his book. 🎥🍿 YOUTUBE: WATCH HERE Links: Matt'…
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Every year, 25 million people download Shaan’s podcast. Sure, he’s a brilliant entrepreneur, investor, and writer, but there’s one skill in particular that keeps Shaan’s audience coming back for more: storytelling. And not the kind of storytelling that feels like an IQ contest. (I know you know what I mean.) Shaan tells stories that burst with aliv…
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Steve is a professional coach and the founder of Downshift — the world's first decelerator. He has left a career in venture, but he remains ambitious, it's just that his ambition is now to have a good, multidimentional life, where he can be a good dad for his kids. Matt has left a traditional path early on to write, travel and discover his own path…
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David Pakman is a political commentator and the host of The David Pakman Show. He joins the podcast to explore a possible paradigm shift in the way he approaches his work and life after the birth of his daughter. 🎥🍿 YOUTUBE: WATCH HERE Links: The David Pakman Show X (Twitter): @dpakman YouTube: David Pakman Show Instagram: david.pakman ⌛TIMESTAMPS …
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Perhaps the best-kept secret of any writer is the ability to find inspiration in unconventional places. And that’s Michael Mauboussin in a nutshell. Investing, business, reading, writing, luck, skill — name a topic he’s passionate about, and he’s found a way to make money from it in his writing. How? By subverting “The Curse of Knowledge.” With his…
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Packy McCormick is proof that writing online can attract real-world opportunities you never dreamed of. He went from 20 Substack subscribers to a $40 million venture fund — and he’s still growing. In this episode, we dive into the three main “how’s” of Packy’s growth. First, he has a distinct, unforgettable style. His business-meets-memes newslette…
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Justin is the co-founder of Transistor, a podcast hosting platform on which The Pathless Path podcast is hosted. Justin is passionate about designing his company so that all the team benefits. He achieves that by making sure that there is always a financial margin as well as a "margin for our emotional health, margin for our physical health, margin…
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Want to build influence with great ideas and simple writing? Look no further than Howard Marks. Most smart people use big words and plastic jargon to reinforce the barrier between themselves and “the common folk.” Howard, on the other hand, breaks down this barrier, and that’s why his ideas are so influential (and why he’s Warren Buffett’s favorite…
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Dom is the lead guide at the VIVIFY Regerative Leadership Program. He helps leaders develop by taking them on an 8-day backpacking expedition in the Sierra mountains. Dom is passionate about preserving the natural world, staying connected to it and practicing aliveness. 🎥🍿 YOUTUBE: WATCH HERE Links: Personal website VIVIFY (Get $500 off if you ment…
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Amor Towles is our modern day F. Scott Fitzgerald. Sure, he’s a critically acclaimed, award-winning novelist (ever heard of “A Gentleman in Moscow”?) but not because he’s cracked the publishing algorithm. Rather than scheming how many books he can sell or how many critics he can impress, his #1 goal is to fulfill his covenant with his reader. “They…
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Rick Lewis could be succinctly described as "a speaker, author & professional consultant", but such technical labelling wouldn't paint a fair picture of who he really is. He describes what he's doing as "intelligent misbehavior". He's public appearances have a much deeper goal than just pure entertainment. Rick is passionate about discovering and b…
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Steven Johnson has studied LLM technology for over 35 years. His consensus? Large Language models and human creativity aren’t at odds. They’re at their best when they work in harmony. Johnson has written thirteen books, many of which explore how tools and technologies expand what humans are capable of and transform societies. He created NotebookLM …
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Kevin is the man behind the Epic Gardening channel. Although he had not read the Pathless Path at the time of the recording of this episode, he seems to be living it with every breath he takes. The only constant thing in his life seems to be that is constatly reinventing himself. From professional poker, gaming, web design, indie consulting, bloggi…
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Chris Dixon is the perfect example of how learning in public can catapult you to success. Come learn how he went from writer to owner, and how you can, too. SPEAKER LINKS: Website: https://cdixon.org/ Twitter: https://twitter.com/cdixon Blog: https://cdixon.substack.com/subscribe Book: https://www.amazon.com/Read-Write-Own-Building-Internet/dp/0593…
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Enroll In The 5th Cohort of Nervous System Mastery: You can get $250 OFF using the code PATHLESS => nsmastery.com Jonny Miller is a dear friend and I've had the privilege to get to know him closely over the past four years on our own journeys. We've lived in Japan, Indonesia, and Mexico together. When we met we were both single but now are both mar…
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It’s the start of 2024 and to celebrate I thought I’d run through some of the best lessons I’ve picked up over the last 12 months. This past year has had over 20 episodes produced so there was a lot to choose from but I ended up settling on 8 insights from some of my favorite conversations both inside and outside of the podcast. Expect to learn how…
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Tiago grew up reading in Barnes and Noble — up to six hours at a time! Now, his bestselling book, Building a Second Brain, is the perfect combination of his favorite genres: self-development, business, and tech. Come learn how Tiago has helped thousands of people unlock their creative potential. SPEAKER LINKS: Website: https://fortelabs.com/ YouTub…
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Tim Urban used to hate writing because he thought it was boring. Now, he has 600,000+ newsletter subscribers, 811,000+ Twitter followers, and one of the most unforgettable (and hilarious) writing styles on the Internet. Come learn how to make your writing fun to read and fun to write. SPEAKER LINKS: Website & Newsletter: https://waitbutwhy.com/ Twi…
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Tim Ferriss has built one of the most lucrative personal brands on the Internet: 2,000,000 newsletter subscribers, 5 #1 New York Times Bestselling books, and 900 million podcast downloads. Come learn his top writing tactics, routines, and habits! SPEAKER LINKS: Website: https://tim.blog/ Newsletter: https://go.tim.blog/5-bullet-friday-1/ Books: htt…
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